1000340-39-5|3-Bromo-4-chloro-7-azaindole| Ambeed

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Quality Control of [ 1000340-39-5 ] Purity: 96% SDS Specification

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Product Details of [ 1000340-39-5 ]

CAS No. :	1000340-39-5
Formula :	C₇H₄BrClN₂
M.W :	231.48
SMILES Code :	BrC1=C[NH]C2=NC=CC(=C12)Cl
MDL No. :	MFCD09880132
InChI Key :	QLGXTRWCWHBPDP-UHFFFAOYSA-N
Pubchem ID :	24729570

Safety of [ 1000340-39-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H319
Precautionary Statements:	P305+P351+P338

Computational Chemistry of [ 1000340-39-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	9
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	48.8
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	28.68 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.74
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.63
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.98
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.32
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.35
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.6

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.54
Solubility	0.0671 mg/ml ; 0.00029 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.88
Solubility	0.303 mg/ml ; 0.00131 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-4.39
Solubility	0.00952 mg/ml ; 0.0000411 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.84 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.66

Application In Synthesis of [ 1000340-39-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 1000340-39-5 ]

[ 1000340-39-5 ] Synthesis Path-Downstream 1~28

1
[ 55052-28-3 ]
[ 1000340-39-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃;	General procedure: 1H-4-chloro-pyrrolo[2,3-b]pyridine (0.763g, 5.0mmol, 1 eq.) was dissolved in DMF (7.5mL, 1.5mL/mmol SM) and NCS (0.701g, 5.25mmol, 1.05 eq.) was added. The resulting mixture was stirred at ambient temperature overnight, protected from light. Then, ice-cold water (25mL, 5mL/mmol SM) was added and the resulting precipitate filtered. The solids were washed four additional times with ice-cold water (4×10mL, 2mL/mmol SM). The solid was collected and dried under high vacuum to give 60 (0.861g, 4.6mmol) as an off-white solid in 92% yield. Melting point: 236C (decomposed). 1H NMR (300MHz, DMSO-d6) delta: 7.21 (d, J=4.2Hz, 1H, H-5), 7.77 (s, 1H, H-2), 8.20 (d, J=4.2Hz, 1H, H-6), 12.35 (br. s, 1H, NH). 13C NMR (75MHz, DMSO-d6) delta: 101.1 (C-3), 113.7 (C-3a), 117.1 (C-5), 125.1 (C-2), 133.8 (C-4), 144.4 (C-6), 147.6 (7a). HRMS (ESI): calculated for C7H5Cl2N2 ([M+H]+): 186.9824, found: 186.9824.
96%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃;	1H-4-chloro-pyrrolo[2,3-b]pyridine (0.765 g, 5 mmol, 1 eq.) was dissolved in DMF (7.5 mL, 1 .5 mL / mmol SM). NBS (0.935 g, 5.25 mmol) was added and the resulting solution was stirred at ambient temperature overnight, protected from light. Then, the solution was poured into ice-cold water (25 mL, 5 mL / mmol SM) and cooled into an ice bath. After ~10min the remaining suspension was filtered and the solid washed four times with 10 mL ice-cold water. Then the solid was collected and dried under high vacuum to give FH5295 as a yellow solid (1 .12 g, 4.8 mmol) in 96 % yield. 1H NMR (300 MHz, DMSO-d6) delta: 7.23 (d, J = 5.1 Hz, 1 H, H-5), 7.81 (d, J = 2.7 Hz, 1 H, H-2), 8.21 (d, J = 5.1 Hz, 1 H, H-6), 12.44 (br s, 1 H, N-H). 13C NMR (75 MHz, DMSO-d6) delta: 85.03 (C-3), 1 14.58 (C-3a), 1 17.13 (C-5), 127.71 (C-2), 134.17 (C-4), 144.18 (C-6), 147.98 (C-7a). HRMS (ESI): calculated for C7H5BrCIN2 ([M+H]+): 230.9319, found: 230.9332. Melting point: 210 C (decomposed).
90.9%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 6h;	A 50ml of flask was charged with 1.52 g of 4-chloro-lH-pyrrolo[2,3-b]pyridine (prepared according to Tetrahedron Letters (2007), 48(9), 1527-1529), 2.7 gNBS and 29ml DMF. The mixture was stirred at rt for 6h. The solvent was evaporated off and purified by chromatography to give the 2.11 g of product, yield: 90.9%.

58%

With N-Bromosuccinimide; In acetone; at 25℃; for 1h;

Step 1 : A solution of C11 (9 g, 59.016 mM) in acetone (60 mL) was slowly added to a solution of N-N-bromosuccinimide (NBS) (10.44 g, 59.01 mM) in acetone (100 mL) at 25C, and the reaction mixture was stirred for 1 hr. at 250C. The solids were collected by filtration, washed with chilled acetone (5OmL), and dried under reduced pressure to provide 3-bromo-4- chloro-1 H-pyrrolo[2,3-b]pyridine (C38) as pale yellow solid. Yield: 7.5g, 58%. 1HNMR(CDCI3) delta: 11.6-11.7 (b, 1 H), 8.1-8.2 (d, 1 H), 7.2-7.4 (s, 1 H), 7.0-7.01 (d, 1 H). Mass:(M+1) 231 calculated for mol. form. C7H4BrCIN2.

References: [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 248 - 267.
[2]Patent: WO2019/76633,2019,A1 .Location in patent: Page/Page column 36; 68; 106.
[3]Journal of Medicinal Chemistry,2019,vol. 62,p. 8847 - 8865.
[4]Patent: WO2008/5457,2008,A2 .Location in patent: Page/Page column 180.
[5]Patent: WO2008/12635,2008,A2 .Location in patent: Page/Page column 90.

2
[ 1000340-39-5 ]
[ 68-12-2 ]
[ 918515-16-9 ]

Yield	Reaction Conditions	Operation in experiment
52%		Step 2: A solution of C38 (8 g, 34.632 mM) in THF (160 mL) was cooled to -780C, treated with n-BuLi (1.6M, 5OmL, 79.63 mM), and stirred for 30 min. at -780C. The cold solution was then slowly treated with DMF (5.056 g, 69.264m M). The reaction mixture was allowed to warm to 25C, stirred for 2 hr., and treated with water (2 mL) to quench the reaction. The reaction mixture was concentrated under reduced pressure and treated with saturated aq. NH4CI (28 mL), and the solids were collected and dried under reduced pressure. The resultant pale yellow solid (3.5g, 52%) was then purified using silica gel column to provide 4-chloro-1 H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (C39). 1HNMR(CDCI3) 8: 12.6-12.8 (b,1 H),10.4-10.6 (s,1 H),8.26-8.3 (d,1 H),8.12-8.18 (s,1 H),7.26-7.3 (d,1 H). Mass:(M+1 ) 181 calculated for mol. form. C8H5CIN2O.

References: [1]Patent: WO2008/12635,2008,A2 .Location in patent: Page/Page column 90.

3
[ 1000340-39-5 ]
[ 287944-16-5 ]
4-chloro-3-(3,6-dihydro-2H-pyran-4-yl)-1H-pyrrolo[ 2,3-b]pyridine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 10071 - 10091.

4
[ 1000340-39-5 ]
4-chloro-3-(3,6-dihydro-2H-pyran-4-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 10071 - 10091.

5
[ 1000340-39-5 ]
3-(3,6-dihydro-2H-pyran-4-yl)-N-((1r,4r)-4-morpholinocyclohexyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-amine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 10071 - 10091.

6
[ 1000340-39-5 ]
N-((1r,4r)-4-morpholinocyclohexyl)-3-(tetrahydro-2hpyran-4-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-amine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 10071 - 10091.

7
[ 1000340-39-5 ]
N-((1r,4r)-4-morpholinocyclohexyl)-3-(tetrahydro-2H-pyran-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-amine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 10071 - 10091.

8
[ 1000340-39-5 ]
[ 182825-17-8 ]
3-bromo-4-chloro-N1-(3′-C-ethynyl-2′,3′-5-tri-O-benzoyl-β-D-ribofuranosyl)pyrrolo[2,3-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%		General procedure: In a flame-dried 2-neck round bottom flask, equipped with a stir bar was added the appropriate heterocycle (1.1 eq.) under argon. Then, anhydrous MeCN (7.5mL/mmol SM) was added, followed by BSA (1.2 eq.). The resulting suspension was stirred at ambient temperature for approximately 10min; after which a clear solution was obtained. Then, glycosyl donor, 18 [15] (1 eq.) was added in one portion, immediately followed by TMSOTf (1.25 eq.). The resulting solution was stirred at ambient temperature for another 15min, and then transferred to a pre-heated oil bath at 80C. Heating was continued until TLC analysis showed full consumption of the starting material (?2-3h), after which the mixture was cooled to ambient temperature. EA was added, and the mixture poured into a sat. aq. NaHCO3 solution. The layers were separated and the water layer extracted twice more with EA. The organic layers were combined, dried over Na2SO4, filtered and evaporated till dryness. The residue was purified by column chromatography 15% EA/Hexanes.

References: [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 248 - 267.

9
[ 271-63-6 ]
[ 1000340-39-5 ]

References: [1]Patent: WO2008/5457,2008,A2 .

10
C₇H₈N₂O [ No CAS ]
[ 1000340-39-5 ]

References: [1]Patent: WO2008/5457,2008,A2 .

11
[ 10025-98-6 ]
[ 1000340-39-5 ]
C₁₄H₈Br₂Cl₄N₄Pd [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; water; at 44.84℃; for 48h;	General procedure: K2PdCl4 and the seven halogeno-derivatives of 7-azaindole(3Cl7AIH, 3Br7AIH, 4Cl7AIH, 4Br7AIH, 5Br7AIH, 3Br4Cl7AIH and5Br3Cl7AIH) were purchased from Sigma-Aldrich.In the syntheses of trans-[PdCl2(L)2] we followed the procedure described earlier for obtaining trans-[PdCl2(7AIH)2] [24] and trans-[PdCl2(7AI3CAH)2] [25]. A hot aqueous solution (10 cm3) of K2PdCl4(0.5 mmol) was mixed with the ethanol solution of the appropriateligand (1.0 mmol, 20 cm3) and stirred at 318 K for 48 h. The obtained pale yellow solids were filtered off,washed with ethanol andthen dried. The results of the elemental analysis are collected in Table 1S in the Supplementary Data.

References: [1]Journal of Molecular Structure,2019,vol. 1181,p. 444 - 454.

12
[ 10025-99-7 ]
[ 1000340-39-5 ]
cis-[PtCl₂(3-bromo-4-chloro-7-azaindole)₂] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; water; at 44.84℃; for 48h;	General procedure: A hot aqueous solution (10 cm3) of K2PtCl4 (0.5 mmol) wasmixed with the ethanol solution of the appropriate ligand(1.0 mmol, 20 cm3) and stirred at 318 K for 48 h. The obtained paleyellow solids were filtered off, washed with ethanol and thendried. The results of the elemental analysis are collected inTable S1 in the Supplementary Data.

References: [1]Polyhedron,2019,vol. 173.

13
[ 1000340-39-5 ]
3-bromo-4-amino-N1-(2’,3’,5’-tri-O-benzoyl-β-D-ribofuranosyl)pyrrolo[2,3-b]pyridine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 8847 - 8865.

14
[ 6974-32-9 ]
[ 1000340-39-5 ]
3-bromo-4-chloro-N1-(2’,3’,5’-tri-O-benzoyl-β-D-ribofuranosyl)pyrrolo[2,3-b]pyridine [ No CAS ]